#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:26:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180299 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/13/7151324.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151324
loop_
_publ_author_name
'Tu, Shu-Jiang'
'Jiang, Bo'
'Zhang, Jun-Yong'
'Jia, Run-Hong'
'Zhang, Yan'
'Yao, Chang-Sheng'
_publ_section_title
;
 Efficient and direct synthesis of poly-substituted
 indeno[1,2-b]quinolines assisted by p-toluene sulfonic acid using
 high-temperature water and microwave heating via one-pot,
 three-component reaction.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3980
_journal_page_last               3985
_journal_paper_doi               10.1039/b611462h
_journal_volume                  4
_journal_year                    2006
_chemical_formula_moiety         'C59 H53 N3 O5 S2'
_chemical_formula_sum            'C59 H53 N3 O5 S2'
_chemical_formula_weight         948.16
_chemical_melting_point          504.0(10)
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.041(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.081(2)
_cell_length_b                   9.4381(14)
_cell_length_c                   35.102(6)
_cell_measurement_reflns_used    3416
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.669
_cell_measurement_theta_min      2.235
_cell_volume                     4993.1(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_sigmaI/netI    0.1222
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            25441
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.9566
_exptl_absorpt_correction_T_min  0.9344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     624
_refine_ls_number_reflns         8790
_refine_ls_number_restraints     62
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1602
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0418P)²+3.9023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.2054
_reflns_number_gt                3935
_reflns_number_total             8790
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b611462h.txt
_cod_data_source_block           060319e
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '503-505' was changed to '504.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        4992.9(13)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7151324
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6521(2) -0.1038(3) 0.18642(9) 0.0475(8) Uani 1 1 d . . .
N2 N 0.0807(2) 0.1273(4) 0.08188(9) 0.0498(9) Uani 1 1 d . . .
N3 N 0.6516(6) 0.3355(6) 0.0651(2) 0.135(2) Uani 1 1 d U . .
O1 O 0.5218(2) 0.1266(4) 0.28988(9) 0.0833(10) Uani 1 1 d . . .
O2 O 0.8553(2) -0.1043(4) 0.29224(10) 0.0791(10) Uani 1 1 d . . .
O3 O 0.2964(2) 0.3737(3) 0.01359(9) 0.0812(10) Uani 1 1 d . . .
O4 O 0.1601(2) -0.1505(3) -0.02383(9) 0.0764(10) Uani 1 1 d . . .
O5 O 0.7734(6) 0.4287(8) 0.0983(3) 0.247(4) Uani 1 1 d U . .
S1 S 0.70408(13) 0.2610(2) 0.21163(6) 0.0726(9) Uani 0.547(6) 1 d P A 1
S2 S 0.30029(17) -0.0857(3) 0.07044(8) 0.0983(13) Uani 0.433(6) 1 d P B 1
C26' C 0.70408(13) 0.2610(2) 0.21163(6) 0.0726(9) Uani 0.453(6) 1 d P A 2
H26' H 0.6670 0.2408 0.1906 0.087 Uiso 0.453(6) 1 calc PR A 2
C54' C 0.30029(17) -0.0857(3) 0.07044(8) 0.0983(13) Uani 0.567(6) 1 d P B 2
H54' H 0.2528 -0.1301 0.0817 0.118 Uiso 0.567(6) 1 calc PR B 2
C1 C 0.5801(2) -0.0350(4) 0.20346(11) 0.0452(10) Uani 1 1 d . . .
C2 C 0.4947(3) -0.0310(4) 0.18049(12) 0.0534(11) Uani 1 1 d . . .
H2A H 0.4677 -0.1242 0.1809 0.064 Uiso 1 1 calc R . .
H2B H 0.5074 -0.0092 0.1542 0.064 Uiso 1 1 calc R . .
C3 C 0.4285(3) 0.0775(5) 0.19480(13) 0.0589(12) Uani 1 1 d . . .
C4 C 0.4249(3) 0.0620(5) 0.23791(13) 0.0686(14) Uani 1 1 d . . .
H4A H 0.3857 0.1341 0.2475 0.082 Uiso 1 1 calc R . .
H4B H 0.3996 -0.0297 0.2437 0.082 Uiso 1 1 calc R . .
C5 C 0.5134(3) 0.0749(5) 0.25808(13) 0.0564(12) Uani 1 1 d . . .
C6 C 0.5905(3) 0.0203(4) 0.23883(11) 0.0463(10) Uani 1 1 d . . .
C7 C 0.6801(3) 0.0349(4) 0.25895(11) 0.0504(11) Uani 1 1 d . A .
H7 H 0.6740 0.0222 0.2864 0.060 Uiso 1 1 calc R . .
C8 C 0.7389(3) -0.0792(4) 0.24392(11) 0.0493(11) Uani 1 1 d . . .
C9 C 0.8224(3) -0.1301(5) 0.26049(13) 0.0565(11) Uani 1 1 d . . .
C10 C 0.8622(3) -0.2214(5) 0.23059(12) 0.0543(11) Uani 1 1 d . . .
C11 C 0.9412(3) -0.2930(5) 0.23103(15) 0.0703(14) Uani 1 1 d . . .
H11 H 0.9793 -0.2910 0.2525 0.084 Uiso 1 1 calc R . .
C12 C 0.9634(3) -0.3683(6) 0.19890(17) 0.0785(16) Uani 1 1 d . . .
H12 H 1.0172 -0.4163 0.1985 0.094 Uiso 1 1 calc R . .
C13 C 0.9065(3) -0.3723(5) 0.16784(15) 0.0738(15) Uani 1 1 d . . .
H13 H 0.9221 -0.4245 0.1466 0.089 Uiso 1 1 calc R . .
C14 C 0.8257(3) -0.3007(5) 0.16689(13) 0.0604(12) Uani 1 1 d . . .
H14 H 0.7876 -0.3049 0.1455 0.072 Uiso 1 1 calc R . .
C15 C 0.8039(3) -0.2233(4) 0.19857(12) 0.0499(11) Uani 1 1 d . . .
C16 C 0.7270(3) -0.1322(4) 0.20868(11) 0.0446(10) Uani 1 1 d . . .
C17 C 0.6484(3) -0.1448(5) 0.14693(11) 0.0476(10) Uani 1 1 d . . .
C18 C 0.6921(3) -0.0622(5) 0.12115(12) 0.0624(12) Uani 1 1 d . . .
H18 H 0.7195 0.0213 0.1292 0.075 Uiso 1 1 calc R . .
C19 C 0.6952(4) -0.1023(7) 0.08382(14) 0.0797(16) Uani 1 1 d . . .
H19 H 0.7250 -0.0471 0.0664 0.096 Uiso 1 1 calc R . .
C20 C 0.6538(4) -0.2253(7) 0.07238(14) 0.0831(17) Uani 1 1 d . . .
H20 H 0.6563 -0.2539 0.0471 0.100 Uiso 1 1 calc R . .
C21 C 0.6090(3) -0.3062(6) 0.09744(15) 0.0791(15) Uani 1 1 d . . .
H21 H 0.5804 -0.3884 0.0891 0.095 Uiso 1 1 calc R . .
C22 C 0.6058(3) -0.2661(5) 0.13546(13) 0.0616(12) Uani 1 1 d . . .
H22 H 0.5754 -0.3208 0.1528 0.074 Uiso 1 1 calc R . .
C23 C 0.3376(3) 0.0492(6) 0.17597(16) 0.0884(17) Uani 1 1 d . . .
H23A H 0.3409 0.0595 0.1489 0.133 Uiso 1 1 calc R . .
H23B H 0.2954 0.1157 0.1854 0.133 Uiso 1 1 calc R . .
H23C H 0.3191 -0.0454 0.1818 0.133 Uiso 1 1 calc R . .
C24 C 0.4564(3) 0.2287(5) 0.18443(15) 0.0809(15) Uani 1 1 d . . .
H24A H 0.4588 0.2372 0.1572 0.121 Uiso 1 1 calc R . .
H24B H 0.5138 0.2486 0.1959 0.121 Uiso 1 1 calc R . .
H24C H 0.4139 0.2950 0.1937 0.121 Uiso 1 1 calc R . .
C25 C 0.7215(3) 0.1785(5) 0.25132(12) 0.0557(12) Uani 1 1 d . . .
C26 C 0.79673(18) 0.2541(3) 0.27748(8) 0.1014(12) Uani 0.547(6) 1 d P A 1
H26 H 0.8221 0.2276 0.3009 0.122 Uiso 0.547(6) 1 calc PR A 1
S1' S 0.79673(18) 0.2541(3) 0.27748(8) 0.1014(12) Uani 0.453(6) 1 d P A 2
C27 C 0.8141(4) 0.3807(7) 0.2528(3) 0.123(3) Uani 1 1 d D . .
H27 H 0.8541 0.4511 0.2604 0.148 Uiso 1 1 calc R A 1
C28 C 0.7702(4) 0.3868(6) 0.2200(2) 0.098(2) Uani 1 1 d D A .
H28 H 0.7775 0.4606 0.2029 0.117 Uiso 1 1 calc R C 1
C29 C 0.1360(3) 0.2449(4) 0.07601(10) 0.0442(10) Uani 1 1 d . . .
C30 C 0.1205(3) 0.3715(4) 0.10033(11) 0.0541(11) Uani 1 1 d . . .
H30A H 0.1125 0.3400 0.1263 0.065 Uiso 1 1 calc R . .
H30B H 0.0659 0.4170 0.0915 0.065 Uiso 1 1 calc R . .
C31 C 0.1951(3) 0.4805(5) 0.10047(11) 0.0563(12) Uani 1 1 d . . .
C32 C 0.2205(3) 0.5062(5) 0.05943(12) 0.0660(13) Uani 1 1 d . . .
H32A H 0.1718 0.5535 0.0459 0.079 Uiso 1 1 calc R . .
H32B H 0.2715 0.5688 0.0594 0.079 Uiso 1 1 calc R . .
C33 C 0.2422(3) 0.3728(5) 0.03885(12) 0.0575(12) Uani 1 1 d . . .
C34 C 0.1953(3) 0.2431(4) 0.04826(10) 0.0466(10) Uani 1 1 d . . .
C35 C 0.2176(3) 0.1104(4) 0.02594(11) 0.0505(11) Uani 1 1 d . B .
H35 H 0.2256 0.1364 -0.0007 0.061 Uiso 1 1 calc R . .
C36 C 0.1407(3) 0.0123(4) 0.02789(11) 0.0483(10) Uani 1 1 d . . .
C37 C 0.1215(3) -0.1105(5) 0.00422(12) 0.0560(11) Uani 1 1 d . . .
C38 C 0.0437(3) -0.1812(5) 0.02147(12) 0.0540(11) Uani 1 1 d . . .
C39 C -0.0008(3) -0.3029(5) 0.01026(13) 0.0663(13) Uani 1 1 d . . .
H39 H 0.0158 -0.3534 -0.0111 0.080 Uiso 1 1 calc R . .
C40 C -0.0706(3) -0.3474(5) 0.03163(15) 0.0700(14) Uani 1 1 d . . .
H40 H -0.1011 -0.4299 0.0249 0.084 Uiso 1 1 calc R . .
C41 C -0.0953(3) -0.2719(5) 0.06240(14) 0.0687(13) Uani 1 1 d . . .
H41 H -0.1424 -0.3041 0.0764 0.082 Uiso 1 1 calc R . .
C42 C -0.0525(3) -0.1487(5) 0.07343(13) 0.0619(12) Uani 1 1 d . . .
H42 H -0.0715 -0.0971 0.0942 0.074 Uiso 1 1 calc R . .
C43 C 0.0185(3) -0.1033(4) 0.05337(11) 0.0497(10) Uani 1 1 d . . .
C44 C 0.0815(3) 0.0184(4) 0.05587(11) 0.0460(10) Uani 1 1 d . . .
C45 C 0.0243(3) 0.1215(4) 0.11417(11) 0.0469(10) Uani 1 1 d . . .
C46 C -0.0548(3) 0.1941(5) 0.11302(12) 0.0585(12) Uani 1 1 d . . .
H46 H -0.0719 0.2473 0.0917 0.070 Uiso 1 1 calc R . .
C47 C -0.1085(3) 0.1869(5) 0.14394(14) 0.0688(13) Uani 1 1 d . . .
H47 H -0.1617 0.2368 0.1437 0.083 Uiso 1 1 calc R . .
C48 C -0.0837(4) 0.1069(6) 0.17495(15) 0.0768(15) Uani 1 1 d . . .
H48 H -0.1202 0.1028 0.1958 0.092 Uiso 1 1 calc R . .
C49 C -0.0060(4) 0.0328(6) 0.17561(13) 0.0776(15) Uani 1 1 d . . .
H49 H 0.0097 -0.0233 0.1966 0.093 Uiso 1 1 calc R . .
C50 C 0.0497(3) 0.0413(5) 0.14497(12) 0.0611(12) Uani 1 1 d . . .
H50 H 0.1034 -0.0071 0.1455 0.073 Uiso 1 1 calc R . .
C51 C 0.1621(4) 0.6175(5) 0.11846(14) 0.0822(16) Uani 1 1 d . . .
H51A H 0.1467 0.5994 0.1443 0.123 Uiso 1 1 calc R . .
H51B H 0.1107 0.6511 0.1042 0.123 Uiso 1 1 calc R . .
H51C H 0.2080 0.6878 0.1181 0.123 Uiso 1 1 calc R . .
C52 C 0.2757(3) 0.4257(6) 0.12348(13) 0.0779(15) Uani 1 1 d . . .
H52A H 0.2597 0.4091 0.1493 0.117 Uiso 1 1 calc R . .
H52B H 0.3225 0.4947 0.1231 0.117 Uiso 1 1 calc R . .
H52C H 0.2957 0.3387 0.1125 0.117 Uiso 1 1 calc R . .
C53 C 0.3014(3) 0.0392(5) 0.04145(11) 0.0552(11) Uani 1 1 d . . .
C54 C 0.40043(14) 0.0928(3) 0.03361(9) 0.1343(15) Uani 0.433(6) 1 d P B 1
H54 H 0.4212 0.1697 0.0200 0.161 Uiso 0.433(6) 1 calc PR B 1
S2' S 0.40043(14) 0.0928(3) 0.03361(9) 0.1343(15) Uani 0.567(6) 1 d P B 2
C55 C 0.4504(4) -0.0282(8) 0.0566(2) 0.121(2) Uani 1 1 d D . .
H55 H 0.5118 -0.0375 0.0571 0.145 Uiso 1 1 calc R B 1
C56 C 0.3999(4) -0.1142(7) 0.07501(18) 0.1001(19) Uani 1 1 d D B .
H56 H 0.4228 -0.1880 0.0899 0.120 Uiso 1 1 calc R D 1
C57 C 0.7336(9) 0.4002(11) 0.0656(3) 0.162(3) Uani 1 1 d U . .
H57 H 0.7601 0.4232 0.0429 0.195 Uiso 1 1 calc R . .
C58 C 0.6102(7) 0.3010(9) 0.0999(3) 0.202(4) Uani 1 1 d U . .
H58A H 0.5539 0.2567 0.0942 0.303 Uiso 1 1 calc R . .
H58B H 0.6013 0.3859 0.1143 0.303 Uiso 1 1 calc R . .
H58C H 0.6474 0.2370 0.1145 0.303 Uiso 1 1 calc R . .
C59 C 0.6156(7) 0.3099(10) 0.0280(3) 0.183(4) Uani 1 1 d U . .
H59A H 0.5588 0.2649 0.0296 0.274 Uiso 1 1 calc R . .
H59B H 0.6549 0.2493 0.0145 0.274 Uiso 1 1 calc R . .
H59C H 0.6088 0.3982 0.0146 0.274 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N1 C1 118.4(3) . . ?
C16 N1 C17 119.9(3) . . ?
C1 N1 C17 121.7(3) . . ?
C44 N2 C29 118.2(3) . . ?
C44 N2 C45 120.8(3) . . ?
C29 N2 C45 120.9(3) . . ?
C57 N3 C59 113.7(8) . . ?
C57 N3 C58 120.6(9) . . ?
C59 N3 C58 125.7(9) . . ?
C28 S1 C25 96.9(3) . . ?
C56 S2 C53 99.7(3) . . ?
C6 C1 N1 119.9(4) . . ?
C6 C1 C2 123.8(3) . . ?
N1 C1 C2 116.3(3) . . ?
C1 C2 C3 113.6(3) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C23 110.5(4) . . ?
C4 C3 C2 108.0(4) . . ?
C23 C3 C2 109.2(4) . . ?
C4 C3 C24 110.1(4) . . ?
C23 C3 C24 108.1(4) . . ?
C2 C3 C24 111.0(3) . . ?
C5 C4 C3 113.6(3) . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
O1 C5 C6 120.4(4) . . ?
O1 C5 C4 121.8(4) . . ?
C6 C5 C4 117.7(4) . . ?
C1 C6 C5 119.5(4) . . ?
C1 C6 C7 122.6(3) . . ?
C5 C6 C7 117.8(4) . . ?
C8 C7 C6 107.5(3) . . ?
C8 C7 C25 109.0(3) . . ?
C6 C7 C25 111.4(3) . . ?
C8 C7 H7 109.6 . . ?
C6 C7 H7 109.6 . . ?
C25 C7 H7 109.6 . . ?
C16 C8 C9 109.4(4) . . ?
C16 C8 C7 122.0(4) . . ?
C9 C8 C7 127.7(4) . . ?
O2 C9 C8 128.0(4) . . ?
O2 C9 C10 126.2(4) . . ?
C8 C9 C10 105.8(4) . . ?
C11 C10 C15 121.5(4) . . ?
C11 C10 C9 130.2(5) . . ?
C15 C10 C9 108.3(4) . . ?
C10 C11 C12 118.6(5) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C13 C12 C11 120.2(5) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 122.0(5) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C15 C14 C13 118.1(5) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C14 C15 C10 119.5(4) . . ?
C14 C15 C16 134.8(4) . . ?
C10 C15 C16 105.8(4) . . ?
C8 C16 N1 122.1(4) . . ?
C8 C16 C15 110.7(4) . . ?
N1 C16 C15 127.2(4) . . ?
C22 C17 C18 120.7(4) . . ?
C22 C17 N1 120.8(4) . . ?
C18 C17 N1 118.5(4) . . ?
C19 C18 C17 120.4(5) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 119.0(5) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C21 C20 C19 121.1(5) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 120.1(5) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 118.7(4) . . ?
C17 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C3 C23 H23A 109.5 . . ?
C3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C3 C24 H24A 109.5 . . ?
C3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 C25 C26 125.7(3) . . ?
C7 C25 S1 121.9(3) . . ?
C26 C25 S1 111.8(3) . . ?
C27 C26 C25 99.0(4) . . ?
C27 C26 H26 130.5 . . ?
C25 C26 H26 130.5 . . ?
C28 C27 C26 116.6(5) . . ?
C28 C27 H27 121.7 . . ?
C26 C27 H27 121.7 . . ?
C27 C28 S1 115.5(5) . . ?
C27 C28 H28 122.2 . . ?
S1 C28 H28 122.2 . . ?
C34 C29 N2 120.5(3) . . ?
C34 C29 C30 123.1(4) . . ?
N2 C29 C30 116.2(3) . . ?
C29 C30 C31 114.3(3) . . ?
C29 C30 H30A 108.7 . . ?
C31 C30 H30A 108.7 . . ?
C29 C30 H30B 108.7 . . ?
C31 C30 H30B 108.7 . . ?
H30A C30 H30B 107.6 . . ?
C32 C31 C30 108.4(4) . . ?
C32 C31 C52 109.4(4) . . ?
C30 C31 C52 110.3(4) . . ?
C32 C31 C51 110.6(4) . . ?
C30 C31 C51 108.7(4) . . ?
C52 C31 C51 109.5(4) . . ?
C33 C32 C31 113.0(4) . . ?
C33 C32 H32A 109.0 . . ?
C31 C32 H32A 109.0 . . ?
C33 C32 H32B 109.0 . . ?
C31 C32 H32B 109.0 . . ?
H32A C32 H32B 107.8 . . ?
O3 C33 C34 120.7(4) . . ?
O3 C33 C32 120.4(4) . . ?
C34 C33 C32 118.8(4) . . ?
C29 C34 C33 119.6(4) . . ?
C29 C34 C35 123.2(4) . . ?
C33 C34 C35 117.2(3) . . ?
C36 C35 C53 110.4(3) . . ?
C36 C35 C34 107.6(3) . . ?
C53 C35 C34 112.1(3) . . ?
C36 C35 H35 108.9 . . ?
C53 C35 H35 108.9 . . ?
C34 C35 H35 108.9 . . ?
C44 C36 C37 109.1(4) . . ?
C44 C36 C35 122.9(4) . . ?
C37 C36 C35 127.8(3) . . ?
O4 C37 C36 128.1(4) . . ?
O4 C37 C38 126.3(4) . . ?
C36 C37 C38 105.6(4) . . ?
C39 C38 C43 121.3(4) . . ?
C39 C38 C37 129.5(4) . . ?
C43 C38 C37 109.2(4) . . ?
C40 C39 C38 118.1(4) . . ?
C40 C39 H39 120.9 . . ?
C38 C39 H39 120.9 . . ?
C41 C40 C39 120.6(5) . . ?
C41 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
C40 C41 C42 121.8(5) . . ?
C40 C41 H41 119.1 . . ?
C42 C41 H41 119.1 . . ?
C43 C42 C41 119.1(4) . . ?
C43 C42 H42 120.5 . . ?
C41 C42 H42 120.5 . . ?
C42 C43 C38 119.0(4) . . ?
C42 C43 C44 135.9(4) . . ?
C38 C43 C44 105.0(3) . . ?
C36 C44 N2 122.4(4) . . ?
C36 C44 C43 111.2(3) . . ?
N2 C44 C43 126.4(3) . . ?
C50 C45 C46 121.2(4) . . ?
C50 C45 N2 119.2(4) . . ?
C46 C45 N2 119.6(4) . . ?
C45 C46 C47 119.0(4) . . ?
C45 C46 H46 120.5 . . ?
C47 C46 H46 120.5 . . ?
C48 C47 C46 120.3(5) . . ?
C48 C47 H47 119.9 . . ?
C46 C47 H47 119.9 . . ?
C49 C48 C47 120.5(4) . . ?
C49 C48 H48 119.8 . . ?
C47 C48 H48 119.8 . . ?
C48 C49 C50 120.0(5) . . ?
C48 C49 H49 120.0 . . ?
C50 C49 H49 120.0 . . ?
C45 C50 C49 119.0(4) . . ?
C45 C50 H50 120.5 . . ?
C49 C50 H50 120.5 . . ?
C31 C51 H51A 109.5 . . ?
C31 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C31 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C31 C52 H52A 109.5 . . ?
C31 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C31 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C35 C53 S2 122.8(3) . . ?
C35 C53 C54 124.5(3) . . ?
S2 C53 C54 112.4(3) . . ?
C55 C54 C53 96.5(3) . . ?
C55 C54 H54 131.7 . . ?
C53 C54 H54 131.7 . . ?
C56 C55 C54 115.4(5) . . ?
C56 C55 H55 122.3 . . ?
C54 C55 H55 122.3 . . ?
C55 C56 S2 115.4(5) . . ?
C55 C56 H56 122.3 . . ?
S2 C56 H56 122.3 . . ?
O5 C57 N3 119.2(12) . . ?
O5 C57 H57 120.4 . . ?
N3 C57 H57 120.4 . . ?
N3 C58 H58A 109.5 . . ?
N3 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
N3 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
N3 C59 H59A 109.5 . . ?
N3 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
N3 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C16 1.376(5) . ?
N1 C1 1.417(4) . ?
N1 C17 1.438(5) . ?
N2 C44 1.375(5) . ?
N2 C29 1.408(5) . ?
N2 C45 1.443(4) . ?
N3 C57 1.378(12) . ?
N3 C59 1.415(9) . ?
N3 C58 1.429(9) . ?
O1 C5 1.221(5) . ?
O2 C9 1.228(5) . ?
O3 C33 1.228(4) . ?
O4 C37 1.221(5) . ?
O5 C57 1.302(10) . ?
S1 C28 1.571(7) . ?
S1 C25 1.609(5) . ?
S2 C56 1.529(6) . ?
S2 C53 1.558(5) . ?
C1 C6 1.351(5) . ?
C1 C2 1.495(5) . ?
C2 C3 1.528(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.523(6) . ?
C3 C23 1.524(6) . ?
C3 C24 1.535(6) . ?
C4 C5 1.494(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.459(5) . ?
C6 C7 1.508(5) . ?
C7 C8 1.502(5) . ?
C7 C25 1.520(6) . ?
C7 H7 0.9800 . ?
C8 C16 1.341(5) . ?
C8 C9 1.449(6) . ?
C9 C10 1.500(6) . ?
C10 C11 1.370(6) . ?
C10 C15 1.402(6) . ?
C11 C12 1.384(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.392(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.497(5) . ?
C17 C22 1.366(6) . ?
C17 C18 1.379(5) . ?
C18 C19 1.366(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.363(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.390(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.602(5) . ?
C26 C27 1.506(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.306(8) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C34 1.346(5) . ?
C29 C30 1.491(5) . ?
C30 C31 1.525(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.523(5) . ?
C31 C52 1.526(6) . ?
C31 C51 1.530(6) . ?
C32 C33 1.494(6) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.457(6) . ?
C34 C35 1.521(5) . ?
C35 C36 1.487(5) . ?
C35 C53 1.516(6) . ?
C35 H35 0.9800 . ?
C36 C44 1.352(5) . ?
C36 C37 1.449(6) . ?
C37 C38 1.495(6) . ?
C38 C39 1.381(6) . ?
C38 C43 1.404(5) . ?
C39 C40 1.381(6) . ?
C39 H39 0.9300 . ?
C40 C41 1.357(6) . ?
C40 H40 0.9300 . ?
C41 C42 1.379(6) . ?
C41 H41 0.9300 . ?
C42 C43 1.370(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.492(5) . ?
C45 C50 1.364(5) . ?
C45 C46 1.376(5) . ?
C46 C47 1.378(6) . ?
C46 H46 0.9300 . ?
C47 C48 1.366(7) . ?
C47 H47 0.9300 . ?
C48 C49 1.365(7) . ?
C48 H48 0.9300 . ?
C49 C50 1.390(6) . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 C54 1.609(5) . ?
C54 C55 1.575(7) . ?
C54 H54 0.9300 . ?
C55 C56 1.300(7) . ?
C55 H55 0.9300 . ?
C56 H56 0.9300 . ?
C57 H57 0.9300 . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C59 H59A 0.9600 . ?
C59 H59B 0.9600 . ?
C59 H59C 0.9600 . ?
